| Montreal Canadiens | |||
| Toronto Maple Leafs | |||
| Detroit Red Wings | |||
| Boston Bruins | |||
| Chicago Blackhawks | |||
| Edmonton Oilers | |||
| Pittsburgh Penguins | |||
| New York Islanders | |||
| New York Rangers | |||
| New Jersey Devils | |||
| Colorado Avalanche | |||
| Los Angeles Kings | |||
| Philadelphia Flyers | |||
| Anaheim Ducks | |||
| Tampa Bay Lightning | |||
| Calgary Flames | |||
| Carolina Hurricanes | |||
| Dallas Stars | |||
| Washington Capitals | |||
| St. Louis Blues | |||
| Year | Winning team | Games | Losing team |
| 1915 | Vancouver Millionaires Frank Patrick | 3–0 | Ottawa Senators |
| 1916 | Montreal Canadiens Newsy Lalonde-playing | 3–2 | Portland Rosebuds |
| 1917 | Seattle Metropolitans Pete Muldoon | 3–1 | Montreal Canadiens |
| 1918 | Toronto Arenas Dick Carroll | 3–2 | Vancouver Millionaires |
| 1919 | Montreal Canadiens Seattle Metropolitans | Series cancelled after the fifth game because of the flu epidemic – Stanley Cup not awarded | |
| 1920 | Ottawa Senators Pete Green | 3–2 | Seattle Metropolitans |
| 1921 | Ottawa Senators Pete Green | 3–2 | Vancouver Millionaires |
| 1922 | Toronto St. Pats George O'Donoghue | 3–2 | Vancouver Millionaires |
| 1923 | Ottawa Senators Pete Green | 2–0 | Edmonton Eskimos |
| 1924 | Montreal Canadiens Léo Dandurand | 2–0 | Calgary Tigers |
| 1925 | Victoria Cougars Lester Patrick | 3–1 | Montreal Canadiens |
| 1926 | Montreal Maroons Eddie Gerard | 3–1 | Victoria Cougars |
| 1927 | Ottawa Senators Dave Gill | 2–0–2 | Boston Bruins |
| 1928 | New York Rangers Lester Patrick-playing | 3–2 | Montreal Maroons |
| 1929 | Boston Bruins Cy Denneny-playing | 2–0 | New York Rangers |
| 1930 | Montreal Canadiens Cecil Hart | 2–0 | Boston Bruins |
| 1931 | Montreal Canadiens Cecil Hart | 3–2 | Chicago Black Hawks |
| 1932 | Toronto Maple Leafs Dick Irvin | 3–0 | New York Rangers |
| 1933 | New York Rangers Lester Patrick | 3–1 | Toronto Maple Leafs |
| 1934 | Chicago Black Hawks Tommy Gorman | 3–1 | Detroit Red Wings |
| 1935 | Montreal Maroons Tommy Gorman | 3–0 | Toronto Maple Leafs |
| 1936 | Detroit Red Wings Jack Adams | 3–1 | Toronto Maple Leafs |
| 1937 | Detroit Red Wings Jack Adams | 3–2 | New York Rangers |
| 1938 | Chicago Black Hawks Bill Stewart | 3–1 | Toronto Maple Leafs |
| 1939 | Boston Bruins Art Ross | 4–1 | Toronto Maple Leafs |
| 1940 | New York Rangers Frank Boucher | 4–2 | Toronto Maple Leafs |
| 1941 | Boston Bruins Cooney Weiland | 4–0 | Detroit Red Wings |
| 1942 | Toronto Maple Hap Day | 4–3 | Detroit Red Wings |
| 1943 | Detroit Red Wings Jack Adams | 4–0 | Boston Bruins |
| 1944 | Montreal Canadiens Dick Irvin | 4–0 | Chicago Black Hawks |
| 1945 | Toronto Maple Leafs Hap Day | 4–3 | Detroit Red Wings |
| 1946 | Montreal Canadiens Dick Irvin | 4–1 | Boston Bruins |
| 1947 | Toronto Maple Leafs Hap Day | 4–2 | Montreal Canadiens |
| 1948 | Toronto Maple Leafs Hap Day | 4–0 | Detroit Red Wings |
| 1949 | Toronto Maple Leafs Hap Day | 4–0 | Detroit Red Wings |
| 1950 | Detroit Red Wings Tommy Ivan | 4–3 | New York Rangers |
| 1951 | Toronto Maple Leafs Joe Primeau | 4–1 | Montreal Canadiens |
| 1952 | Detroit Red Wings Tommy Ivan | 4–0 | Montreal Canadiens |
| 1953 | Montreal Canadiens Dick Irvin | 4–1 | Boston Bruins (8, 3–5) |
| 1954 | Detroit Red Tommy Ivan | 4–3 | Montreal Canadiens (14, 7–6) |
| 1955 | Detroit Red Jimmy Skinner | 4–3 | Montreal Canadiens (15, 7–7) |
| 1956 | Montreal Toe Blake | 4–1 | Detroit Red Wings (14, 7–7) |
| 1957 | Montreal Canadiens Toe Blake | 4–1 | Boston Bruins (9, 3–6) |
| 1958 | Montreal Canadiens Toe Blake | 4–2 | Boston Bruins (10, 3–7) |
| 1959 | Montreal Canadiens Toe Blake | 4–1 | Toronto Maple Leafs (16, 9–7) |
| 1960 | Montreal Canadiens Toe Blake | 4–0 | Toronto Maple Leafs (17, 9–8) |
| 1961 | Chicago Black Rudy Pilous | 4–2 | Detroit Red Wings (15, 7–8) |
| 1962 | Toronto Maple Punch Imlach | 4–2 | Chicago Black Hawks (6, 3–3) |
| 1963 | Toronto Maple Punch Imlach | 4–1 | Detroit Red Wings (16, 7–9) |
| 1964 | Toronto Maple Punch Imlach | 4–3 | Detroit Red Wings (17, 7–10) |
| 1965 | Montreal Canadiens Toe Blake | 4–3 | Chicago Black Hawks (7, 3–4) |
| 1966 | Montreal Canadiens Toe Blake | 4–2 | Detroit Red Wings (18, 7–11) |
| 1967 | Toronto Maple Punch Imlach | 4–2 | Montreal Canadiens (23, 14–8) |
| 1968 | Montreal Canadiens Toe Blake | 4–0 | St. Louis Blues ( W ) (1, 0–1) |
| 1969 | Montreal Canadiens Claude Ruel | 4–0 | St. Louis Blues ( W ) (2, 0–2) |
| 1970 | Boston Bruins Harry Sinden | 4–0 | St. Louis Blues ( W ) (3, 0–3) |
| 1971 | Montreal Canadiens Al MacNeil | 4–3 | Chicago Black Hawks ( W ) (8, 3–5) |
| 1972 | Boston Bruins Tom Johnson | 4–2 | New York Rangers ( E ) (8, 3–5) |
| 1973 | Montreal Canadiens Scotty Bowman | 4–2 | Chicago Black Hawks ( W ) (9, 3–6) |
| 1974 | Philadelphia Flyers Fred Shero | 4–2 | Boston Bruins ( E ) (13, 5–8) |
| 1975 | Philadelphia Flyers Fred Shero | 4–2 | Buffalo Sabres ( PW ) (1, 0–1) |
| 1976 | Montreal Canadiens Scotty Bowman | 4–0 | Philadelphia Flyers ( CC ) (3, 2–1) |
| 1977 | Montreal Canadiens Scotty Bowman | 4–0 | Boston Bruins ( PW ) (14, 5–9) |
| 1978 | Montreal Canadiens Scotty Bowman | 4–2 | Boston Bruins ( PW ) (15, 5–10) |
| 1979 | Montreal Canadiens Scotty Bowman | 4–1 | New York Rangers ( CC ) (9, 3–6) |
| 1980 | New York Islanders Al Arbour | 4–2 | Philadelphia Flyers ( CC ) (4, 2–2) |
| 1981 | New York Islanders Al Arbour | 4–1 | Minnesota North Stars ( PW ) (1, 0–1) |
| 1982 | New York Islanders Al Arbour | 4–0 | Vancouver Canucks ( CC ) (1, 0–1) |
| 1983 | New York Islanders Al Arbour | 4–0 | Edmonton Oilers ( CC ) (1, 0–1) |
| 1984 | Edmonton Oilers Glen Sather | 4–1 | New York Islanders ( PW ) (5, 4–1) |
| 1985 | Edmonton Oilers Glen Sather | 4–1 | Philadelphia Flyers ( PW ) (5, 2–3) |
| 1986 | Montreal Canadiens Jean Perron | 4–1 | Calgary Flames ( CC ) (1, 0–1) |
| 1987 | Edmonton Oilers Glen Sather | 4–3 | Philadelphia Flyers ( PW ) (6, 2–4) |
| 1988 | Edmonton Oilers Glen Sather | 4–0 | Boston Bruins ( PW ) (16, 5–11) |
| 1989 | Calgary Flames Terry Crisp | 4–2 | Montreal Canadiens ( PW ) (33, 23–9) |
| 1990 | Edmonton Oilers John Muckler | 4–1 | Boston Bruins ( PW ) (17, 5–12) |
| 1991 | Pittsburgh Penguins Bob Johnson | 4–2 | Minnesota North Stars ( CC ) (2, 0–2) |
| 1992 | Pittsburgh Penguins Scotty Bowman | 4–0 | Chicago Blackhawks ( CC ) (10, 3–7) |
| 1993 | Montreal Canadiens Jacques Demers | 4–1 | Los Angeles Kings ( CC ) (1, 0–1) |
| 1994 | New York Rangers Mike Keenan | 4–3 | Vancouver Canucks ( WC ) (2, 0–2) |
| 1995 | New Jersey Devils Jacques Lemaire | 4–0 | Detroit Red Wings ( WC ) (19, 7–12) |
| 1996 | Colorado Avalanche Marc Crawford | 4–0 | Florida Panthers ( EC ) (1, 0–1) |
| 1997 | Detroit Red Wings Scotty Bowman | 4–0 | Philadelphia Flyers ( EC ) (7, 2–5) |
| 1998 | Detroit Red Wings Scotty Bowman | 4–0 | Washington Capitals ( EC ) (1, 0–1) |
| 1999 | Dallas Stars Ken Hitchcock | 4–2 | Buffalo Sabres ( EC ) (2, 0–2) |
| 2000 | New Jersey Devils Larry Robinson | 4–2 | Dallas Stars ( WC ) (4, 1–3) |
| 2001 | Colorado Avalanche Bob Hartley | 4–3 | New Jersey Devils ( EC ) (3, 2–1) |
| 2002 | Detroit Red Wings Scotty Bowman | 4–1 | Carolina Hurricanes ( EC ) (1, 0–1) |
| 2003 | New Jersey Devils Pat Burns | 4–3 | Mighty Ducks of Anaheim |
| 2004 | Tampa Bay Lightning John Tortorella | 4–3 | Calgary Flames |
| 2005 | Season cancelled due to the 2004–05 NHL lockout. | ||
| 2006 | Carolina Hurricanes Peter Laviolette | 4–3 | Edmonton Oilers |
| 2007 | Anaheim Ducks Randy Carlyle | 4–1 | Ottawa Senators |
| 2008 | Detroit Red Wings Mike Babcock | 4–2 | Pittsburgh Penguins |
| 2009 | Pittsburgh Penguins Dan Bylsma | 4–3 | Detroit Red Wings |
| 2010 | Chicago Blackhawks Joel Quenneville | 4–2 | Philadelphia Flyers |
| 2011 | Boston Bruins Claude Julien | 4–3 | Vancouver Canucks |
| 2012 | Los Angeles Kings Darryl Sutter | 4–2 | New Jersey Devils |
| 2013 | Chicago Blackhawks Joel Quenneville | 4–2 | Boston Bruins |
| 2014 | Los Angeles Kings Darryl Sutter | 4–1 | New York Rangers |
| 2015 | Chicago Blackhawks Joel Quenneville | 4–2 | Tampa Bay Lightning |
| 2016 | Pittsburgh Penguins Mike Sullivan | 4–2 | San Jose Sharks |
| 2017 | Pittsburgh Penguins Mike Sullivan | 4–2 | Nashville Predators |
| 2018 | Washington Capitals Barry Trotz | 4–1 | Vegas Golden Knights |
| 2019 | St. Louis Blues Craig Berube | 4–3 | Boston Bruins |
| 2020 | Tampa Bay Lightning Jon Cooper | 4–2 | Dallas Stars |
| 2021 |
